(S,S)-Phg-LeuOMe | 1246611-00-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S,S)-Phg-LeuOMe
• 英文别名: methyl (2S)-2-[[(2S)-2-amino-2-phenylacetyl]amino]-4-methylpentanoate
• CAS: 1246611-00-6
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: UYTOQHCKWUMXEJ-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,S)-Phg-LeuOMe 在 盐酸 、 ethylene dichloride hydrochloride 、 C₆H₅N₃O*Cl^(1-) 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones

  摘要：

  Phosphothreonine (pThr)-embedded peptide catalysts are found to mediate the reductive amination of 3-amidocyclohexanones with divergent selectivity. The choice of peptide sequence can be used to alter the diastereoselectivity to favor either the cis-product or trans-product, which are obtained in up to 93:7 er. NMR studies and DFT calculations are reported and indicate that both pathways rely on secondary interactions between substrate and catalyst to achieve selectivity. Furthermore, catalysts appear to accomplish a parallel kinetic resolution of the substrates. The facility for phosphopeptides to tune reactivity and access multiple products in reductive aminations may translate to the diversification of complex substrates, such as natural products, at numerous reactive sites.

  DOI：

  10.1021/acs.joc.8b00207
• 作为产物：
  描述：

  N-(叔丁氧羰基)-L-2-苯甘氨酸 在 盐酸 、 ethylene dichloride hydrochloride 、 C₆H₅N₃O*Cl^(1-) 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (S,S)-Phg-LeuOMe
  参考文献：
  名称：

  Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones

  摘要：

  Phosphothreonine (pThr)-embedded peptide catalysts are found to mediate the reductive amination of 3-amidocyclohexanones with divergent selectivity. The choice of peptide sequence can be used to alter the diastereoselectivity to favor either the cis-product or trans-product, which are obtained in up to 93:7 er. NMR studies and DFT calculations are reported and indicate that both pathways rely on secondary interactions between substrate and catalyst to achieve selectivity. Furthermore, catalysts appear to accomplish a parallel kinetic resolution of the substrates. The facility for phosphopeptides to tune reactivity and access multiple products in reductive aminations may translate to the diversification of complex substrates, such as natural products, at numerous reactive sites.

  DOI：

  10.1021/acs.joc.8b00207

文献信息

• Oxalyl retro-peptide gelators. Synthesis, gelation properties and stereochemical effects
  作者：Janja Makarević、Milan Jokić、Leo Frkanec、Vesna Čaplar、Nataša Šijaković Vujičić、Mladen Žinić

  DOI：10.3762/bjoc.6.106

  日期：——

  In this work we report on gelation properties, self-assembly motifs, chirality effects and morphological characteristics of gels formed by chiral retro-dipeptidic gelators in the form of terminal diacids (1a-5a) and their dimethyl ester (1b-5b) and dicarboxamide (1c-5c) derivatives. Terminal free acid retro-dipeptides (S,S)-bis(LeuLeu) 1a, (S,S)-bis(PhgPhg) 3a and (S,S)-bis(PhePhe) 5a showed moderate

  在这项工作中，我们报告了末端二酸（1a-5a）及其二甲酯（1b-5b）和二甲酰胺形式的手性反二肽胶凝剂形成的凝胶的凝胶特性、自组装基序、手性效应和形态特征(1c-5c)衍生物。末端游离酸逆向二肽 (S,S)-bis(LeuLe​​u) 1a、(S,S)-bis(PhgPhg) 3a 和 (S,S)-bis(PhePhe) 5a 对高极性水表现出中等至优异的胶凝作用/DMSO 和水/DMF 溶剂混合物。掺入不同氨基酸(S,S)-(LeuPhg) 2a 和(S,S)-(PhgLeu) 4a 的逆向肽没有显示出凝胶化或显示出非常弱的凝胶化。外消旋和单一对映体胶凝剂的胶凝效果不同。与纯手性 (S,S)-1c 相比，异手性 (S,R)-1c 非对映异构体能够固定多达 10 倍和 4 倍体积的二氯甲烷/DMSO 和甲苯/DMSO 溶剂混合物。基于非对映异构二酯 (S,S)-1b/(S,R)-1b 和二酸